methyl (Z)-2-[(dimethoxyphosphoryl)methyl]-3-phenyl-2-propenoate | 123347-23-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (Z)-2-[(dimethoxyphosphoryl)methyl]-3-phenyl-2-propenoate
• 英文别名: (Z)-methyl 2-((dimethoxyphosphoryl)methyl)-3-phenylacrylate；methyl 2-[(dimethylphosphoryl)methyl]-3-phenyl-2-propenoate；methyl (Z)-2-(dimethoxyphosphorylmethyl)-3-phenylprop-2-enoate
• CAS: 123347-23-9；123347-22-8
• 化学式: C₁₃H₁₇O₅P
• 分子量: 284.249
• InChiKey: OJSAMYLYMKMMBN-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-[(dimethoxyphosphoryl)methyl]-3-phenyl-2-propenoate 在 [Rh(cod)2]SbF6 、 (S)-(-)-[(S)-2-diphenylphosphinoferrocenyl](N,N-dimethylamino)(2-diphenylphosphinophenyl)methane 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、2.0 MPa 条件下， 反应 24.0h， 生成 methyl 2-[(dimethoxyphosphoryl)methyl]-3-phenyl-2-propionate
  参考文献：
  名称：

  Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acid derivatives via Rh-catalyzed asymmetric hydrogenation

  摘要：

  The commercially available ferrocene-based diphosphine ligand (S-c,S-Fc)-TaniaPhos was found to be highly effective in the Rh-catalyzed asymmetric hydrogenation of 3-aryl-2-(phosphonomethyl)propenates. Excellent enantioselectivity (90-98% ee) and high catalytic activity (S/C up to 1000) have been achieved, which represents the best results reported so far. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.12.002
• 作为产物：
  描述：

  生成 methyl (Z)-2-[(dimethoxyphosphoryl)methyl]-3-phenyl-2-propenoate
  参考文献：
  名称：

  Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acid derivatives via Rh-catalyzed asymmetric hydrogenation

  摘要：

  The commercially available ferrocene-based diphosphine ligand (S-c,S-Fc)-TaniaPhos was found to be highly effective in the Rh-catalyzed asymmetric hydrogenation of 3-aryl-2-(phosphonomethyl)propenates. Excellent enantioselectivity (90-98% ee) and high catalytic activity (S/C up to 1000) have been achieved, which represents the best results reported so far. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.12.002

文献信息

• Enantioselective Rh-Catalyzed Hydrogenation of 3-Aryl-2-phosphonomethylpropenoates by a New Class of Chiral Ferrocenyl Diphosphine Ligands
  作者：Dao-Yong Wang、Xiang-Ping Hu、Chuan-Jin Hou、Jun Deng、Sai-Bo Yu、Zheng-Chao Duan、Jia-Di Huang、Zhuo Zheng

  DOI：10.1021/ol9012469

  日期：2009.8.6

  A new class of chiral ferrocenyl diphosphine ligands with an imidazole ring, (Rc,SFc)-ImiFerroPhos, has been prepared from acylferrocenes through a five-step transformation and successfully applied in the Rh-catalyzed asymmetric hydrogenation of various 3-aryl-substituted 2-phosphonomethylpropenoates, in which a series of chiral 3-phosphono-2-arylmethylpropanoic acid derivatives were achieved in ee

  新型的具有咪唑环的手性二茂铁基二膦配体（R c，S Fc）-ImiFerroPhos通过五步转化由酰基二茂铁制备，并成功地用于Rh催化的各种3-芳基-不对称加氢反应取代的2-膦酰基甲基丙酸酯，其中一系列手性3-膦酰基-2-芳基甲基丙酸衍生物的ee值高达98％。
• Simple and Advantageneous Stereoselective Synthesis of (<i>Z</i>)-Allyl Phosphonates Starting from Baylis–Hillman Adducts
  作者：Biswanath Das、Nisith Bhunia、Kongara Damodar

  DOI：10.1080/00397911.2011.561396

  日期：2012.9

  Baylis-Hillman adducts 3-hydroxyl-2-methylene alkanoates have been converted in one pot into the corresponding (Z)-allyl phosphonates by treatment with FeCl3 and trialkyl phosphites in toluene under reflux. The products are formed in excellent yields (88-98%) within 1-1.5 h. The process is highly convenient and efficient, cost-effective, and remarkably stereoselective.
• Asymmetric Synthesis of 2-Alkyl-3-phosphonopropanoic Acids via P−C Bond Formation and Hydrogenation
  作者：Pallavi A. Badkar、Nigam P. Rath、Christopher D. Spilling

  DOI：10.1021/ol701500s

  日期：2007.8.1

  Allylic acetates, formed by the acetylation of Baylis Hillman adducts, undergo addition of phosphorus nucleophiles to give stereoselectively the Z-unsaturated esters. TFA cleavage of the tert-butyl ester and asymmetric hydrogenation of the unsaturated acid yields the phosphono alkyl propanoic acid moiety, commonly found in phosphonate- and phosphinate-based enzyme inhibitors.
• Synthesis and reactions of 3-substituted-2-phosphomethyl acrylates
  作者：William R. Schoen、William H. Parsons

  DOI：10.1016/s0040-4039(00)80716-9

  日期：1988.1